| Revision as of 11:44, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 461179236 of page Pentobarbital for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 03:06, 12 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Short-acting barbiturate}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Distinguish|phenobarbital|Sodium thiopental{{!}}sodium pentothal}} |
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{{Use dmy dates|date=August 2023}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 464198399 |
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| Verifiedfields = changed |
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| image = Pentobarbital 2d.svg |
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| Watchedfields = changed |
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| image_class = skin-invert-image |
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| verifiedrevid = 456483472 |
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| width = 115 |
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| IUPAC_name = 5-Ethyl-5-(1-methylbutyl)-2,4,6(1''H'',3''H'',5''H'')-pyrimidinetrione |
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| image = Pentobarbital-2D-skeletal.png |
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| image2 = Pentobarbital ball-and-stick.png |
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| image_class2 = bg-transparent |
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| width = 180 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Nembutal |
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| Drugs.com = {{drugs.com|monograph|pentobarbital}} |
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| Drugs.com = {{drugs.com|monograph|pentobarbital}} |
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| MedlinePlus = a682416 |
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| MedlinePlus = a682416 |
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| DailyMedID = Pentobarbital |
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| pregnancy_category = D (]) |
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| pregnancy_AU = C |
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| legal_status = ]: ] (oral and ]); ] (rectal), ]: Class B Controlled Substance |
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| routes_of_administration = Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for ]) |
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| routes_of_administration = ], ], ], ] |
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| class = ] |
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| ATC_prefix = N05 |
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| ATC_suffix = CA01 |
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| ATC_supplemental = {{ATCvet|N51|AA01}} |
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| legal_AU = S8 |
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| legal_AU_comment = , S4 for IV preparations<ref>{{cite web | url=https://www.legislation.gov.au/F2024L00589/latest/text | title=Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024 | date=30 May 2024 }}</ref> |
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| legal_BR = B1 |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=16 August 2023 |publisher=] |language=pt-BR |publication-date=4 April 2023}}</ref> |
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| legal_CA = Schedule IV |
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| legal_DE = Anlage III |
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| legal_UK = Class B |
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| legal_US = Schedule II |
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| legal_UN = Psychotropic Schedule III |
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| legal_status = Rx-only |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 70-90% oral; 90% rectal |
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| bioavailability = 70–90% (oral); 90% (rectal) |
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| protein_bound = 20-45% |
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| protein_bound = 20–45% |
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| metabolism = ] |
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| metabolism = ] |
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| elimination_half-life = 15-48 hours |
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| elimination_half-life = 15–48 hours |
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| excretion = ] |
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| excretion = ] |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 5480 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 76-74-4 |
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| CAS_number = 76-74-4 |
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| ATC_prefix = N05 |
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| ATC_suffix = CA01 |
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| ATC_supplemental = {{ATCvet|N51|AA01}} |
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| PubChem = 4737 |
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| PubChem = 4737 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00312 |
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| DrugBank = DB00312 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| IUPAC_name = 5-Ethyl-5-(1-methylbutyl)-2,4,6(1''H'',3''H'',5''H'')-pyrimidinetrione |
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| C=11 | H=18 | N=2 | O=3 |
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| C=11 | H=18 | N=2 | O=3 |
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| molecular_weight = 226.27 |
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| smiles = O=C1NC(=O)NC(=O)C1(C(C)CCC)CC |
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| smiles = O=C1NC(=O)NC(=O)C1(C(C)CCC)CC |
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| InChI = 1/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16) |
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| InChIKey = WEXRUCMBJFQVBZ-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16) |
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| StdInChI = 1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16) |
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| StdInChIKey = WEXRUCMBJFQVBZ-UHFFFAOYSA-N |
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| StdInChIKey = WEXRUCMBJFQVBZ-UHFFFAOYSA-N |
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}} |
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}} |
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'''Pentobarbital''' (US) or '''pentobarbitone''' (British and Australian) is a short-acting ] typically used as a ], a ], and to control ]s in emergencies.<ref name=":0" /> It can also be used for short-term treatment of ] but has been largely replaced by the ] family of drugs. |
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In high doses, pentobarbital causes death by ]. It is used for ] and is used by some US states and the ] for ] of convicted criminals by ].<ref name="auto">{{cite news | vauthors = Palmer K |date= 28 October 2013 |title=Ohio says it will switch to new drugs for executions |url=https://www.reuters.com/article/us-usa-executions-ohio-idUSBRE99R0SK20131028/ |publisher=] }}</ref> In some countries and states, it is also used for ].<ref name="ABC" /><ref name="Stuff" /> |
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Pentobarbital was widely ] beginning in the late 1930s and sometimes known as "yellow jackets" due to the yellow color of Nembutal-branded capsules.<ref>{{Cite journal |last=Cozanitis |first=Dimitri A |date=December 2004 |title=One hundred years of barbiturates and their saint |journal=Journal of the Royal Society of Medicine |volume=97 |issue=12 |pages=594–598 |doi=10.1177/014107680409701214 |issn=0141-0768 |pmc=1079678 |pmid=15574863}}</ref> Pentobarbital in oral (pill) form is not commercially available.<ref name="auto" />{{failed verification|date=November 2024}} |
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Pentobarbital was developed by ] and {{ill|Donalee L. Tabern|de}} at ] in 1930. |
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==Uses== |
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===Medical=== |
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Typical applications for pentobarbital are ], short term ], ], ] treatment, and control of ] in emergencies.<ref name=":0">{{cite web | title=Nembutal sodium- pentobarbital sodium injection | website=DailyMed | date=31 December 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5c380ab0-4386-48b6-80ab-ca594b23bc74 | access-date=29 January 2020}}</ref> Abbott Pharmaceutical discontinued manufacture of their Nembutal brand of Pentobarbital capsules in 1999, largely replaced by the benzodiazepine family of drugs. |
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Pentobarbital can reduce intracranial pressure in ], treat traumatic brain injury and induce coma in ] patients.<ref name="monograph">{{cite web | url= https://www.drugs.com/monograph/pentobarbital.html | format= Monograph | title= Pentobarbital | publisher= AHFS | website= Drugs.com| access-date=}}</ref> Pentobarbital-induced coma has been advocated in patients with ] ] to ].<ref name="pentobarbital">{{cite journal | vauthors = Stravitz RT, Kramer AH, Davern T, Shaikh AO, Caldwell SH, Mehta RL, Blei AT, Fontana RJ, McGuire BM, Rossaro L, Smith AD, Lee WM | display-authors = 6 | title = Intensive care of patients with acute liver failure: recommendations of the U.S. Acute Liver Failure Study Group | journal = Critical Care Medicine | volume = 35 | issue = 11 | pages = 2498–2508 | date = November 2007 | pmid = 17901832 | doi = 10.1097/01.CCM.0000287592.94554.5F | s2cid = 11924124 }}</ref> |
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Pentobarbital is also used as a veterinary anesthetic agent.<ref>{{cite web |title=Pentobarbital |url=https://www.drugs.com/international/pentobarbital.html |access-date= |website=Drugs.com |publisher=}}</ref> |
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=== Euthanasia and assisted suicide=== |
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Pentobarbital can cause death when used in high doses. It is used for ] for humans as well as animals. It is taken alone, or in combination with complementary agents such as ], in commercial ] injectable solutions.<ref name="ABC">{{cite news | vauthors = Chaar B, Sami Isaac S | url= https://www.abc.net.au/news/2017-10-20/assisted-dying-what-is-need-from-drugs-for-voluntary-euthanasia/9069896|title=Euthanasia drugs: What is needed from medications for assisted deaths?| website= abc.net.au| publisher= ]|date=20 October 2017|quote=Both secobarbital capsules and pentobarbital (usually known as the brand name, Nembutal) liquid — (not to be mistaken for epilepsy medication phenobarbital) have been used either alone or in combination for physician-assisted suicide or euthanasia. They are also used in injectable forms for animal euthanasia.|access-date=22 September 2021}}</ref><ref name="Stuff">{{cite web | vauthors = Martin H | url= https://www.stuff.co.nz/national/health/euthanasia-debate/300073069/euthanasia-referendum-what-drugs-are-used-in-assisted-dying-and-how-do-they-work|title=Euthanasia referendum: What drugs are used in assisted dying, and how do they work?|website=]|date=13 August 2020|quote=In Australia, most people will ingest the lethal dose of pentobarbital as a drink – a white powder mixed with about 30 millilitres of a liquid suspension. However, in cases where the person is too ill to ingest the medication themselves, a doctor or nurse practitioner could administer the dose, under the proposed Act.|access-date=22 September 2021}}</ref> |
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In the ], pentobarbital is part of the standard protocol for ] for self-administration by the patient.<ref name="netherlands">{{cite web | vauthors = Köhler W |date=23 November 2000 |title=Euthanica |url=http://retro.nrc.nl/W2/Lab/Profiel/Euthanasie/euthanatica.html |work=Euthanesia Dossier |publisher=NRC Webpagina's |language=nl}}</ref> It is given in liquid form, in a solution of sugar syrup and ], containing 9 grams of pentobarbital. This is preceded by an ] to prevent vomiting.<ref name="netherlands" /> |
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It is taken by mouth for physician-assisted death in the United States states of Oregon, Washington, Vermont, and California (as of January 2016).<ref name= ongoing2011>{{cite journal | vauthors = Fass J, Fass A | title = Physician-assisted suicide: ongoing challenges for pharmacists | journal = American Journal of Health-System Pharmacy | volume = 68 | issue = 9 | pages = 846–849 | date = May 2011 | pmid = 21515870 | doi = 10.2146/ajhp100333 }}</ref><ref name="pph">{{cite book |title=The Peaceful Pill Handbook |pages=137 | vauthors = Philip N, Stewart F |isbn=0978878809 |year= 2006 |publisher=Exit International US Ltd |url= https://books.google.com/books?id=bNp3cyJImJwC&pg=PA137 | via= Google Books}}</ref> The oral dosage of pentobarbital indicated for physician-assisted suicide in Oregon is typically 10 g of liquid.<ref name="ongoing2011" /><ref name="pph" /> |
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In ], sodium pentobarbital is administered to the patient ]. Once administered, sleep is induced within 30 seconds, and the heart stops beating within 3 minutes.<ref>{{Citation |title=Assisted dying in Switzerland |url=https://www.youtube.com/watch?v=NDcRLCpCro4 |publication-date=15 February 2022 |type=Video |at=39:00 min - 41:19 min |publisher=Dying with Dignity in Canada |language=en |access-date=6 November 2022}}</ref> Oral administration is also used. A Swiss pharmacist reported in 2022 that the dose for assisted suicide had been raised to 15 grams because with lower doses death was preceded by a coma of up to 10 hours in some cases.<ref>{{Cite web | vauthors = Keller M | date = 22 May 2022 |title=Assistierter Suizid in der Schweiz - Sterben auf Wunsch | trans-title = Assisted suicide in Switzerland - dying on request |url=https://www.deutschlandfunk.de/assistierte-sterbehilfe-schweiz-suizid-begleitung-100.html |access-date=6 November 2022 |language=de | work = Deutschlandfunk | publisher = Deutschlandradio }}</ref> |
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=== Execution === |
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Pentobarbital has been used or considered as a substitute for the barbiturate ] used for ] by ] in the United States when that drug became unavailable.<ref name="Mears_2012">{{cite news | vauthors = Mears B | url= http://www.cnn.com/2012/05/21/politics/states-lethal-injection-drugs | title= States urge feds to help import lethal injection drugs | publisher= CNN | date= 21 May 2012}}</ref> In 2011 the U.S. manufacturer of sodium thiopental stopped production, and importation of the drug proved impossible. Pentobarbital was used in a U.S. execution for the first time in December 2010 in Oklahoma, as part of a three-drug protocol.<ref name="Mears_2012" /> In March 2011 pentobarbital was used for the first time as the sole drug in a U.S. execution, in Ohio. Since then several states as well as the federal government have used pentobarbital for lethal injections; some use three-drug protocols and others use pentobarbital alone. |
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Pentobarbital is produced by the Danish company ]. Use of the drug for executions is illegal under Danish law, and when this was discovered, after public outcry in Danish media, Lundbeck stopped selling it to US states that impose the ] and prohibited US distributors from selling it to any customers, such as state authorities, that practice or participate in executions of humans.<ref>{{cite magazine | vauthors = Sanburn J | url=https://nation.time.com/2013/08/07/the-hidden-hand-squeezing-texas-supply-of-execution-drugs/ |magazine=] | date=7 August 2013 | title=The Hidden Hand Squeezing Texas' Supply of Execution Drugs}}</ref> |
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Texas began using the single-drug pentobarbital protocol for executing death-row inmates on 18 July 2012,<ref name="bbc2012">{{cite news |url=https://www.bbc.co.uk/news/world-us-canada-18897310 |title=Texas executes Yokamon Hearn with pentobarbitol | date= 18 July 2012 | work= bbc.co.uk | publisher= BBC News |access-date=9 December 2017 }}</ref> because of a shortage of ], a muscle paralytic previously used as one component of a three-drug cocktail.<ref name="bbc2012" /> In October 2013, ] changed its protocol to allow for pentobarbital from a ] to be used in a lethal dose for executions.<ref>{{Cite news | vauthors = Lewis A |url=https://www.bbc.com/news/world-us-canada-24935868|title=Lethal injection: Secretive US states resort to untested drugs |work= bbc.co.uk | publisher= BBC News |date=15 November 2013 |language=en-GB|access-date= 17 March 2016}}</ref> It was first used in November 2013.<ref>{{Cite news | vauthors = Salter J | url= https://news.yahoo.com/missouri-executes-serial-killer-franklin-122636393.html | archive-url = https://web.archive.org/web/20131123124201/https://news.yahoo.com/missouri-executes-serial-killer-franklin-122636393.html | archive-date = 23 November 2013 | title= Missouri executes serial killer Franklin | date= 20 November 2013 |publisher=Yahoo News }}</ref><ref>{{Cite news | vauthors = Martin SK | url= http://www.christianpost.com/news/joseph-paul-franklin-executed-first-mo-inmate-killed-using-pentobarbital-109150 | title= Joseph Paul Franklin Executed; First MO Inmate Killed Using Pentobarbital | date= 20 November 2013 |publisher= | work= ]}}</ref> |
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According to a December 2020 ] article, by 2017 the federal ] (BOP), in discussion with then Attorney General ], had begun to search for suppliers of pentobarbital to be used in lethal injections. The BOP was aware that the use of pentobarbital as their "new drug choice" would be challenged in the courts because some lawyers had said that "pentobarbital would flood prisoners' lungs with froth and foam, inflicting pain and terror akin to a death by drowning." BOP claimed that these concerns were unjustified and that their two expert witnesses asserted that the use of pentobarbital was "humane".<ref>{{Cite news| vauthors = Arnsdorf I | title= Inside Trump and Barr's Last-Minute Killing Spree| work= ProPublica| access-date= 11 January 2021 |date=23 December 2020| url= https://www.propublica.org/article/inside-trump-and-barrs-last-minute-killing-spree?token=KV1iffz1F9fK0zFiLSbSXrhlEeeah5Bq}}</ref> On 25 July 2019, ] ] directed the federal government to resume capital punishment after 16 years.<ref>{{Cite news | vauthors = Williams P, Arkin D |url=https://www.nbcnews.com/politics/justice-department/ag-barr-orders-reinstatement-federal-death-penalty-n1034451 |date=25 July 2019 |title=AG Barr orders reinstatement of the federal death penalty|publisher=] }}</ref> The federal protocol provides for intravenous administration of two syringes each containing 2.5 grams of pentobarbital sodium followed by a saline flush.<ref>, U.S. Department of Justice, 25 July 2019</ref> |
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== Pharmacology == |
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=== Pharmacodynamics === |
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Like other barbiturates, pentobarbital binds to the barbiturate-binding site on the ]. This action increases the duration of ion-channel opening. At high doses, pentobarbital is capable of opening the ion channel in the absence of ].<ref>{{cite book | vauthors = Baer AB, Holstege CP | chapter = Barbiturates, Long-Acting |date = January 2005 | title = Encyclopedia of Toxicology | edition = Second |pages=209–210 | veditors = Wexler P |place=New York |publisher=Elsevier |language=en |doi=10.1016/b0-12-369400-0/00104-6 |isbn=978-0-12-369400-3 }}</ref> |
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=== Pharmacokinetics === |
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Pentobarbital undergoes ] in the liver and possibly the intestines.<ref name=first-pass>{{cite journal | vauthors = Knodell RG, Spector MH, Brooks DA, Keller FX, Kyner WT | title = Alterations in pentobarbital pharmacokinetics in response to parenteral and enteral alimentation in the rat | journal = Gastroenterology | volume = 79 | issue = 6 | pages = 1211–1216 | date = December 1980 | pmid = 6777235 | doi = 10.1016/0016-5085(80)90915-4 | doi-access = free }}</ref> |
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==Drug interactions== |
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Administration of ], ]s, ]s, ]s, other ]s, and other ] will cause possible additive effects.<ref name=monograph/> |
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==Chemistry== |
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Pentobarbital is synthesized by methods analogous to that of ], the only difference being that the alkylation of α-ethylmalonic ester is carried out with 2-bromopentane in place of 1-bromo-3-methylbutane to give pentobarbital.<ref>{{cite journal | vauthors = Volwiler EH, Tabern DL | title = 5,5-Substituted Barbituric Acids1 | journal = Journal of the American Chemical Society | volume = 52 | issue = 4 | pages = 1676–1679 | year = 1930 | doi = 10.1021/ja01367a061 }}</ref><ref>Kaiserliches Patentamt German imperial patent, D.R.P. 293163 (16 July 1916), Bayer& Co</ref><ref>{{ cite patent | country = GB | number = 650354 | status = patent | inventor = Wilde BE, Balaban IE | assign1 = Geigy | title = Improvements in the manufacture of substituted barbituric and thiobarbituric acids | gdate = 21 February 1951 | pridate = 1948-09-29}}</ref> |
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Pentobarbital can occur as a ] but is usually ] as the sodium ], pentobarbital sodium. The free acid is only slightly ] in water and in ]<ref name="pubchem">{{cite web |title=Pentobarbital Compound summary | id = CID4737 |url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4737 |work=PubChem |publisher= U.S National Library of Medicine }}</ref><ref>{{cite web |title=FR1972_08_25_17226 |url=https://www.fda.gov/ohrms/dockets/98fr/FR1972_08_25_17226(9861).pdf | archive-url = https://web.archive.org/web/20160311073649/https://www.fda.gov/ohrms/dockets/98fr/FR1972_08_25_17226(9861).pdf | archive-date = 11 March 2016 |publisher=Food and Drug Administration}}</ref> while the sodium salt shows better solubility. |
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==Society and culture== |
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''Pentobarbital'' is the ], ], ], and ] while ''pentobarbitone'' is a former AAN and BAN. |
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One brand name for this drug is ''Nembutal'', coined by John S. Lundy, who started using it in 1930, from the structural formula of the ]—Na (sodium) + ] + ] + ] + ] (common ] for ]s).<ref name="Nembutal">{{cite journal | vauthors = Fosburgh LC | title = From this point in time: some memories of my part in the history of anesthesia--John S. Lundy, MD | journal = AANA Journal | volume = 65 | issue = 4 | pages = 323–328 | date = August 1997 | pmid = 9281913 }}</ref> Nembutal is trademarked and manufactured by the Danish pharmaceutical company ] (now produced by Akorn Pharmaceuticals) is the only injectable form of pentobarbital approved for sale in the United States. |
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] |
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] discontinued its Nembutal brand of pentobarbital capsules in 1999, largely replaced by the benzodiazepine family of drugs. Abbott's Nembutal, known on the streets as "yellow jackets", was widely abused.<ref>{{cite news |date=1 July 2011 | vauthors = Jolly D |title=Danish Company Blocks Sale of Drug for U.S. Executions |url= https://www.nytimes.com/2011/07/02/world/europe/02execute.html |newspaper=] |access-date=20 November 2013}}</ref><ref>{{Cite book |url=https://www.worldcat.org/oclc/4557439 |title=High Times Encyclopedia of Recreational Drugs |date=1978 |publisher=Stonehill | vauthors = Aldrich MR, Ashley R, Horowitz M |isbn=0-88373-082-0 |location=New York |pages=243 |oclc=4557439}}</ref> They were available as 30, 50, and 100 mg capsules of yellow, white-orange, and yellow colors, respectively.<ref>{{Cite book |url=https://www.worldcat.org/oclc/4636066 |title=Physicians' Desk Reference |date=1979 |publisher=Medical Economics Co |isbn=0-87489-999-0 |edition=33rd |location=Oradell, New Jersey |pages=403 |oclc=4636066}}</ref> |
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== References == |
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{{Reflist}} |
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{{Anticonvulsants}} |
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{{Hypnotics and sedatives}} |
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